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Abstract Background There is less attention to assessing how health services meet the expectations of private health insurance (PHI) actors, clients, insurers, and providers in developing countries. Interdependently, the expectations of each actor are stipulated during contract negotiations (duties, obligations, and privileges) in a PHI arrangement. Complementary service roles performed by each actor significantly contribute to achieving their expectations. This study assessed the role of PHI in meeting the expectations of clients, insurers, and providers in Kampala. Lessons from this study may inform possible reviews and improvements in Uganda’s proposed National Health Insurance Scheme (NHIS) to ensure NHIS service responsiveness. Methods This study employed a qualitative case-study design. Eight (8) focus group discussions (FGDs) with insured clients and nine (9) key informant interviews (KIIs) with insurer and provider liaison officers between October 2020 and February 2021 were conducted. Participants were purposively selected from eligible institutions. Thematic analysis was employed, and findings were presented using themes with corresponding anonymized narratives and quotes. Results Client-Provider, Client-Insurer, and Provider-Insurer expectations were generally not met. Client-provider expectations: Although most facilities were clean with a conducive care environment, clients experienced low service care responsiveness characterized by long waiting times. Both clients and providers received inadequate feedback about services they received and delivered respectively, in addition to prompt care being received by a few clients. For client-insurer expectations, under unclear service packages, clients received low-quality medicines. Lastly, for provider-insurer expectations, delayed payments, selective periodic assessments, and inadequate orientation of clients on insurance plans were most reported. Weak coordination between the client-provider and insurer did not support delivery processes for responsive service. Conclusion Health care service responsiveness was generally low. There is a need to commit resources to support the setting up of clearer service package orientation programs, and efficient monitoring and feedback platforms. Uganda’s proposed National Health Insurance Act may use these findings to: Inform its design initiatives focusing on operating under realistic expectations, investment in quality improvement systems and coordination, and efficient and accountable client care relationships.